Dorset Boltholes with Enclosed Gardens

In a self-catering cottage with an enclosed garden you and your family can enjoy some added privacy and security. Help contain lively legs and take a look at our luxury portfolio in Dorset. At Classic Cottages, we want your whole experience to be the best it can be and handpick all of our cottages onto our books. Find your cottage today for dreams tomorrow. Read more

Whether you are looking for family-friendly accommodation or a dog-friendly cottage with an enclosed garden, we have a selection of properties available in Dorset for you to choose from. To give you some added reassurance, let your kids play and your dog sniff around in a garden offering more security. You'll be able to relax knowing your loved ones are nearby.

Cottages with Enclosed Gardens in Dorset 

Across Dorset we have a range of beautiful self-catering cottages of all shapes and sizes. Priding ourselves on marketing only the finest self-catering accommodation around, we want your holiday in Dorset to be the best it can be. Browse our selection of 18 available retreats with enclosed gardens and find your perfect one. The holiday of a lifetime is but moments away. 

18 retreats with enclosed gardens in Dorset

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £558

3 bedroom, dog friendly self catering cottage near Bridport, Dorset.


Barn Owls Cottage, a semi-detached cottage converted from an 18th Century stone barn, has retained much of its original character with inset fossils and huge oak beams. The kitchen...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £558

  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £606

3 bedroom, dog friendly holiday cottage near Lyme Regis, Dorset.


Imagine spending a week in a fabulous former dairyman’s cottage with all mod-cons! This very stylishly furnished, yet quirky, semi-detached cottage is in the village of Morcombelak...

  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £606

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £618

3 bedroom holiday cottage in Corfe Castle, Dorset.


You will be completely spoilt for choice in this stunning part of Dorset – along the Jurassic Coast and within very easy reach are Lulworth Cove and Durdle Door with their famous c...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £618

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £659

4 bedroom holiday cottage near the beach in Studland, Dorset.


The Isle of Purbeck is a stunning Area of Outstanding Natural Beauty between Poole and Swanage boasting one of the most spectacular coastlines in Dorset. Sunnyholme, an extremel...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £659

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £679

3 bedroom holiday cottage in Corfe Castle, Dorset.


Situated in the popular Dorset village of Corfe Castle, on the Studland peninsula, close to the coast, this Grade II Listed picture-book cottage enjoys views of the spectacular Nat...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £679

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £740

3 bedroom, dog friendly cottage near the beach in Christchurch.


Avon Beach, Christchurch Harbour, the New Forest National Park and the Jurassic Coast are all nearby to this recently renovated holiday bolthole. The cool shades of blue and the pl...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £740

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1043 *

5 bedroom, dog friendly cottage near the beach near Lyme Regis.


Less than half a mile from the World Heritage Jurassic Coast, The Old Manor House is a beautiful 16th Century, Grade II Listed house, full of character with a delightful enclosed g...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1043 *

  • Sleeps 8 + 3 cots in 2 properties
  • Changeover Fri

7 nights from £779


West Hembury Farm is situated in an Area of Outstanding Natural Beauty; a walker's paradise. Just four miles from the bustling market town of Bridport, and a short drive to the Wo...

  • Sleeps 8 + 3 cots in 2 properties
  • Changeover Fri

7 nights from £779